The chapter reports on an empirical study of promoting digital transformation (DX) within local communities, focusing on Shizuoka Prefecture. Known for its rich natural environment and proactive disaster prevention and mitigation initiatives, including preparations for Mt. Fuji eruptions and the anticipated Nankai Trough earthquake, the area serves as a prime example of integrating advanced technologies into community resilience strategies. The study aimed to explore the advancement of DX, particularly in disaster prevention and mitigation, through a series of workshops conducted over two fiscal years. The initial workshop identified several challenges in promoting DX, leading to the development of Proof of Concepts (PoCs) utilizing generative AI and cloud technology. The second workshop facilitated deeper engagement with residents and local government officials, providing valuable insights into the early stages of societal implementation. Building on this foundation, the focus shifted to West Izu in Shizuoka Prefecture, incorporating perspectives from sociology and folklore experts and utilizing graph data structures to further evolve the PoCs. These activities culminated in recommendations for multi-stakeholder processes and the establishment of digital governance frameworks necessary for promoting DX effectively within local communities. This approach demonstrated the critical role of tailored technological applications and collaborative governance in addressing the unique needs and challenges of local settings.